Diastereoselective Total Synthesis of (±)‐Schindilactone A

Xiao, Qing; Ren, Weiwu; Chen, Zhixing; Sun, Tao; Li, Yong; Ye, Qin‐Da; Gong, Jianxian; Meng, Fanke; You, Lin; Liu, Yifan; Zhao, Mi; Xu, Letian; Shan, Zhen‐Hua; Shi, Ying; Tang, Yefeng; Chen, Jiahua; Yang, Zhen

doi:10.1002/ange.201103088

Cited by 52 publications

(5 citation statements)

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“…Noticeably, rubriflordilactone B was known as one of the more active family members. Fascinatingly, rubriflordilactone A exhibited limited antiviral activity [58] . The development of complementary Pd‐and Co‐catalyzed methods to attain the tricyclic arylsilane derivatives that are suitable for elaboration into the CDE ring systems of rubriflordilactones A and B was described by Anderson et al .…”

Section: Applications Of Cobalt‐catalyzed Reactions In the Total Synt...mentioning

confidence: 99%

“…In addition, their striking frameworks show a formidable synthetic challenge, first met in 2011 by Yong et al . in the formation of schindilactone A [58] . This innovative accomplishment was completed by a sophisticated asymmetric construction of rubriflordilactone A 54 .…”

Section: Applications Of Cobalt‐catalyzed Reactions In the Total Synt...mentioning

confidence: 99%

“…Yang et al . in 2011 reported the total synthesis of schindilactone A 50 was started from ketone 47 and after 12 steps gave enyne 48 [58] . Then, undecan‐2‐one scaffold in 49 was constructed in a cis ‐fused method through thiourea/Co‐catalyzed PKR [59] of enyne 48 .…”

Section: Applications Of Cobalt‐catalyzed Reactions In the Total Synt...mentioning

confidence: 99%

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Applications of Cobalt‐Catalyzed Reactions in the Total Synthesis of Natural Products

et al. 2022

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Cobalt‐catalyzed has attracted much attention, and being used to the total synthesis of a wide range of naturally occurring compounds having complex structures. The chemist of natural products is a distinct part of chemical research that has been important in the history of chemistry, pharmacology, the finding of substances in initial preclinical drug discovery research, and also the understanding of folk medicine. The Cobalt‐catalyzed reaction has frequently been used as a key step (steps) in the total synthesis of natural products and targeted complex bioactive molecules. In this review, we want to show the application of cobalt‐catalyzed reactions in the synthesis of natural products having biological activities from 2000 till date.

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Section: Applications Of Cobalt‐catalyzed Reactions In the Total Synt...mentioning

confidence: 99%

Section: Applications Of Cobalt‐catalyzed Reactions In the Total Synt...mentioning

confidence: 99%

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Applications of Cobalt‐Catalyzed Reactions in the Total Synthesis of Natural Products

et al. 2022

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“…Following the pioneering synthesis of schinortriterpenoid schindilactone A [4a] by Yang [ 4 ] and co‐workers in 2011, the elegant total syntheses of several other members were achieved in the past decade, including Yang's total syntheses of propindilactone G [4b] (2015), 19‐dehydroxyl arisandilactone A [4c] (2017), lancifodilactone G acetate [4d] (2018), and pre‐schisanartanin C [4e] (2019); Li's total syntheses [ 5 ] of rubriflordilactone A [5a] (2014), rubriflordilactone B [5b] (2016), and pseudo ‐rubriflordilactone B [5c] (2019); Anderson's total syntheses [ 6 ] of rubriflordilactone A [6a,6b] (2015), rubriflordilactone B [6c] (2019), and pseudo ‐rubriflordilactone B [6c] (2019); Tang's total syntheses [ 7 ] of schilancitrilactones B and C [7a] (2015), schilancitrilactone A [7b] (2017), and schilancidilactones A and B [7b] (2017); and Ding's total synthesis of atrop‐schiglautone A [8] (2018).…”

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confidence: 99%

Development of Biomimetic Synthesis of Propindilactone G^†

Wang

Chen

et al. 2020

Chin. J. Chem.

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of main observation and conclusion The natural product propindilactone G is a complex Schisandra nortriterpenoid with a unique 5/5/7/6/5 pentacyclic framework. This full paper describes the development of concise biomimetic synthesis of propindilactone G from a known steroid lactone. The key C19-OH intermediate was synthesized via Breslow and Suárez radical remote C-H functionalizations. Wagner-Meerwein rearrangement was subsequently utilized for the expansion of the B ring. To invert the configuration of the C10 tertiary alcohol, an intramolecular peroxide cyclization catalyzed by BF3•Et2O was devised. The 5/5 fused lactone system was then assembled in a biomimetic transesterification/oxa-Michael addition sequence. Our work should provide experimental support for the proposed biosynthetic pathway and facilitate investigation of the biological activities of propindilactone G.

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“…[3] In 2011, Yang and co-workers reported the first total synthesis of schindilactone A. [4] Recently,the group of Li disclosed the first asymmetric total synthesis of rubriflordilactone A. [5] Herein we report our efforts on developing anew strategy to solve the chemical synthesis of 1 and 2,a nd apathway for the synthesis of their analogues and derivatives for medicinal studies.Our retrosynthetic analysis is shown in Scheme 1.…”

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Total Synthesis of Schilancitrilactones B and C

Wang

Tang

2015

Angewandte Chemie

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The first total syntheses of schilancitrilactones B and C have been accomplished in 17 steps (longest linear sequence) from commercially available materials. Key steps include an intramolecular radical cyclization to provide the seven-membered ring, late-stage iodination, and an intermolecular radical addition reaction to complete the total synthesis.Schilancitrilactones B and C (1 and 2; Figure 1) [1] were isolated in 2012 by Sun and co-workers from the stems of Schisandra Lancifolia, which have been used in traditional Chinese medicine for the treatment of neurasthenia and related diseases.[2] Preliminary biological assays indicated that schilancitrilactone C showed biological activities for inhibiting HIV-1 while schilancitrilactone B was not bioactive. The structures of these compounds were striking in that they contain a 5/7/5/5/5-fused pentacyclic ring system bearing nine stereogenic centers. In addition, the three cis-fused fivemembered rings (rings C-E), all with the envelope conformations, and seven contiguous chiral centers (including two quaternary centers) form a structurally rigid tricyclic ring system. Construction of these highly oxygenated unique motifs remains challenging. Herein, we present the first total synthesis of schilancitrilactones B and C. The key steps include the successful implementation of an intramolecular radical cyclization to prepare a seven-member ring, late-stage iodination, and an intermolecular radical CÀC bond formation.

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Diastereoselective Total Synthesis of (±)‐Schindilactone A

Cited by 52 publications

References 39 publications

Applications of Cobalt‐Catalyzed Reactions in the Total Synthesis of Natural Products

Applications of Cobalt‐Catalyzed Reactions in the Total Synthesis of Natural Products

Development of Biomimetic Synthesis of Propindilactone G^†

Total Synthesis of Schilancitrilactones B and C

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Diastereoselective Total Synthesis of (±)‐Schindilactone A

Cited by 52 publications

References 39 publications

Applications of Cobalt‐Catalyzed Reactions in the Total Synthesis of Natural Products

Applications of Cobalt‐Catalyzed Reactions in the Total Synthesis of Natural Products

Development of Biomimetic Synthesis of Propindilactone G†

Total Synthesis of Schilancitrilactones B and C

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Product

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Development of Biomimetic Synthesis of Propindilactone G^†